


Lucky

by bloodandcream



Series: The more the merrier [27]
Category: Supernatural
Genre: Alternate Universe, Castiel and Anna are only step-siblings, Double Penetration in Two Holes, Multi, PWP, Spanking, Threesome - F/M/M
Language: English
Status: Completed
Published: 2015-07-10
Updated: 2015-07-10
Packaged: 2018-04-08 14:30:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,022
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4308756
Author URL: https://archiveofourown.org/users/bloodandcream/pseuds/bloodandcream
Summary: <blockquote class="userstuff">
              <p>Castiel and Anna hadn’t always had a relationship quite so intimate. They were glued to each other’s sides as soon as he moved on campus, but it wasn’t until a little friendly sibling rivalry to see who could seduce Dean Winchester first had ended in Dean propositioning the both of them, at the same time, that they crossed the last and only boundary line standing between them.</p>
            </blockquote>





	Lucky

His ass was bright pink and warm to the touch when Anna spread her hand across the smooth skin. There was the distinct outline of her hand with splayed fingers across the right ass cheek, but most of his skin had blended into an even pink from being worked over.

Kneading into the skin that must be tingling from the spanking by now, Anna scraped him lightly with her nails and lay a few light swats down.

“You’ve been such a good boy, do you think you deserve a treat?”

Castiel grunted when she emphasized her question with a hard slap. He squirmed on her lap, rubbing his hard cock on her thigh.

“P-please…”

If she hit him lightly, he sighed little breathy noises through his nose. If she hit him hard enough, he’d grunt and ball the pale blue sheets in his fist. He always pushed his ass up higher when she hit him hard.

College was fun.

Anna had been so home sick and lonely during her first year, but then her little brother decided to follow her to the same school. She and Castiel had been nearly inseparable since he was adopted at eleven years old. Although he was only a year younger than her, she was always the one that got them in to trouble.

He spread his thighs and canted his ass back, begging for more. Anna pressed down between his shoulder blades, holding him against her lap as she raised her hand and swung with all her force, the loud crack of her hand on his ass a sharp sudden noise. He moaned and pressed his face in to the sheets, toes curling down gripping. Anna’s hand was starting to hurt too, throbbing and warm.

Needy little grunts from across the room distracted her.

Dean was staring wide eyed, licking his lips, hard cock in his hand palming himself slowly as he watched.

Castiel and Anna hadn’t always had a relationship quite so intimate. They were glued to each other’s sides as soon as he moved on campus, but it wasn’t until a little friendly sibling rivalry to see who could seduce Dean Winchester first had ended in Dean propositioning the both of them, at the same time, that they crossed the last and only boundary line standing between them.

Who could say no to Dean.

Broad freckled shoulders, teeth biting as plump lips, his pretty cock was wet at the tip as he squeezed and slowly dragged his fist up the length of it.

“What do you think Dean, has he been a good boy?”

“Fuck yeah, christ, his ass is bright red.”

Soothing her hands over the tender skin, Ann nudged a thigh up to get Castiel’s attention, pushing gently against his side. He was trembling finely, a sheen of perspiration on his tan skin.

“Go on then, I’ll join you two in a minute.”

Castiel whimpered and nodded, crawling off the bed and across the floor to Dean. They were both naked but Anna was still wearing her black lace panties and bra. She had a private bedroom at the sorority house, it was small but nice. The carpet was plush and cream colored, walls a faint pink color. Her twin bed wasn’t large enough to host threesomes, but there was more than enough room on the floor.

Unclasping her bra and pushing down her panties, Dean was watching her eagerly as Cas started going down on him. Anna sifted through her top dresser drawer to find a few things. Setting a bottle of lube and condoms on the small table beside her bed, she dropped a pink jelly dildo on the floor next to Castiel. The purple plug she coated, lifting one leg to rest her foot on the bed with her back facing Dean as she pushed it inside herself. Bending over, rubbing her fingers down the length of her pussy she teased the plug in her ass and twisted it around a few times before straightening.

Dropping to her knees on the floor she nudged Castiel’s legs a little wider apart. The plug was a pleasant stretch, not stimulating enough for her tastes but she’d be loose enough to take Dean after she was done playing with Castiel.

He made the dirtiest noises when she gave him a spanking if he was choking on a cock too.

Dean had his fingers threaded through Castiel’s hair, hips pumping forward to fuck his face. Castiel arched his back, spreading his legs wider for Anna as he sucked noisily, wet squelching and sloppy. Slicking up the pink dildo, ridged with veins and a head that was vaguely realistic, Anna pressed the rounded end of the toy to Castiel’s hole and held on to his hip as she popped it inside.

She didn’t have any idea he’d been doing this to himself since he was fourteen with vegetables out of the fridge.

His body opened easily around the toy, hips pushing back to take it in further. Dean cradled his face, cock pressed into his mouth but still, fingers running along his jaw as Anna worked the toy in. Mostly to the base, she held it there with one hand and raised the other to smack down hard on his still red blushing ass. Castiel jerked between them, shoulder blades twitching back as he rolled his shoulders, muscles going tense before he sagged. His deep throated grunts were muffled around Dean’s cock, fingers scrabbling against the carpet.

Anna scratched livid furrows down his back and ass and thighs, smiling sweetly at Dean. “Do you wanna fuck his ass while I ride him?”

“Mmm, wanna get inside you tonight sweetheart.”

Anna distractedly pumped the toy in and out of her step-brother. “Both at the same time?”

Dean started thrusting his hips shallowly, slack jawed pleasure on his face, “Fuck yeah.”

Rocking the toy in deep and twisting it around, Anna gave Castiel a few more slaps while Dean fucked his face. He rocked between them, push-pull, hips rhythmic as he rolled his back and Anna wondered just when her gawky teenage brother had turned in to this. All lithe muscle and tan skin, still a little awkward but such a slut if you slapped him around a little.

Rubbing the pad of her thumb around the ring of muscle as she pulled the toy out, taking her time to finger him for a little while, Anna pressed her fingers into the slick heat of his body and down. Smooth velvet walls clenched around her as he twitched and groaned. It would be so easy to make him climax like this, Dean fucking his throat raw, her fingers focusing on that sweet spot, but she wanted something else from him tonight.

Pulling back, giving one more hard crack to his ass, Anna stood up and considered the next move. Dean pulled out of Castiel’s mouth, spit trailing between his dick and swollen pink lips. He looked at her, licked his lips and asked, “Edge of the bed?”

Anna nodded, bending forward to reach between her legs and pull the plug out. Setting it aside on a tissue with the dildo, Dean was already up and across the room. Castiel sat up and rested against his heels, looking at her with wild eyes and a bright flush to his cheeks. His cock was bouncing in his lap, tapping up against his belly, mouth hanging open as he panted.

She pointed a finger at him, “You stay on the floor.”

Dean sat on the edge of the bed, feet still planted on the floor, and patted his lap. He grabbed her hips and turned her around to face Castiel, tugging her down to straddle his thighs. Anna passed him a condom and the lube, perched on his lap holding herself up on her knees as Castiel scooted closer to the bed. Dean’s strong arms wrapped around her waist and pulled her down onto his cock, thick length stretching her ass and his calloused fingers were sliding down between her legs to rub her clit.

Whimpering, head fallen back on Dean’s shoulder, Anna grasped the wrist of his hand still pressed to her belly and nudged her hips in little circles as he stretched her pressing deep. Her muscles seized at the suddenness but it didn’t take long before the flash of pain ebbed to pleasure. Panting, Anna waved Castiel closer. Beyond words, she grabbed his hair and shoved his face between her thighs. Dean spread his legs wider so Castiel could wedge in between them, lapping at her pussy as Dean fucked her ass.

Wet tongue hot and slick pushing up in to her, Anna moaned and ground forward against Castiel’s face. Dean’s hands bracketed her waist and lifted her up a little so she could hold still and let Castiel press his fingers inside as he sucked on her clit, and Dean could lift his hips up off the bed and fuck into her ass, working together. He held her in place as Anna gripped into Castiel’s hair and swiveled her hips, trying to push back and shove forward at the same time. Tight heat coiled in her belly, and it didn’t take long after Castiel crooked his fingers inside her moving with Dean’s thrusts, she climaxed with a stuttered pleading feeling her body seize and quake.

Flushed hot and lax with pleasure, Anna fell easily onto Dean’s lap again as Castiel pulled back. He was rolling a condom on as Dean pulled Anna’s hair over one shoulder and kissed at her neck, fingers toying with a nipple, hand squeezing a breast and she arched into the contact.

“Hold on for the ride for the ride sweetheart.”

“Hm?”

Blinking stupidly, Anna craned her head back to look at Dean. She was wet against the inside of her thighs, still clenched around him, heart beating fast with arousal as he circled both arms tight around her waist at the same time that Castiel caught her legs and they lifted her up like she was a feather. She wouldn’t think it should be so easy, to hold her aloft in between them, even though she were much smaller. But Dean held her steady as she wrapped her legs around Castiel’s waist as he adjusted his stance and thrust up into her pussy.

Her step-brother’s wide hands held under her thighs as he fucked into her alongside Dean who was standing behind her. Trapped between the two of them, hard muscle and heat, Anna cried out and clutched at Castiel’s shoulders. It was blissful, being so full, stretched wide around the two of them fucking her together.

Dean’s hand pressed flat against her belly, he rubbed his scratchy jaw down the soft skin of her neck. “Fuck I can feel your brother in there, sliding up next to me.”

Anna groaned, head fallen back on Dean’s shoulder, unable to do any more than dig her nails in to Castiel’s shoulders. They held her up and found their pace together, building up a rhythm and driving her mad with it.

It was almost too swift a climb to another climax, jostled between the two of them, overwhelmed, it crested and broke and her body shuddered through as they kept moving faster, harder, another building on the ripples of the last, then another, a series of orgasms cresting through the lingering aftershocks.

Bodies sliding together easily with sweat, Dean and Castiel strained against her, fingers digging in harshly to her hips and belly as they tensed nearly at the same time, squashing her between their weight. Castiel was the first to slip out, eyes glazed and body weaving. Dean set her gently back down to the floor but her legs were shaking too much to stand upright anyway.

Anna collapsed on the bed in a fit of giggles. Curling on to a side and watching the two boys tie off their condoms and throw them away, turn to each other with open hands and lips kissing sweetly in the afterglow, she couldn’t help smiling widely and wondering when she got so lucky.


End file.
